3-(4-Fluoro-phenyl-sulfon-yl)-2-methyl-naphtho-[1,2-b]furan.

In the title compound, C(19)H(13)FO(3)S, the 4-fluoro-phenyl ring makes a dihedral angle of 68.59 (5)° with the mean plane of the naphtho-furan fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O, C-H⋯F and C-H⋯π inter-actions. The crystal structure also exhibits aromatic π-π inter-actions between the central benzene and the outer benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.650 (3) Å].

Related literature

For the pharmacological activity of naphtho­furan compounds, see: Einhorn et al. (1984 ▶); Hranjec et al. (2003 ▶); Mahadevan & Vaidya (2003 ▶). For our previous structural studies of related 3-aryl­sulfonyl-2-methyl­naphtho­[1,2-b]furan derivatives, see: Choi et al. (2008 ▶).

Experimental

Crystal data

C19H13FO3S

M = 340.35

Orthorhombic,

a = 8.1456 (3) Å

b = 18.4472 (5) Å

c = 10.3618 (4) Å

V = 1557.00 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.30 × 0.25 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.664, T max = 0.746

7603 measured reflections

2719 independent reflections

2502 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.075

S = 1.05

2719 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 830 Friedel pairs

Flack parameter: 0.09 (7)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048361/sj5062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048361/sj5062Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H13FO3S	F(000) = 704
Mr = 340.35	Dx = 1.452 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3161 reflections
a = 8.1456 (3) Å	θ = 2.3–27.5°
b = 18.4472 (5) Å	µ = 0.23 mm−1
c = 10.3618 (4) Å	T = 173 K
V = 1557.00 (9) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.12 mm

Bruker SMART APEXII CCD diffractometer	2719 independent reflections
Radiation source: rotating anode	2502 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.2°
φ and ω scans	h = −10→4
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −23→22
Tmin = 0.664, Tmax = 0.746	l = −10→13
7603 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.1905P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2719 reflections	Δρmax = 0.25 e Å−3
218 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 830 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.09 (7)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.52554 (5)	0.41581 (2)	0.52995 (6)	0.02619 (12)
F1	1.07897 (19)	0.56345 (10)	0.29185 (19)	0.0694 (5)
O1	0.46264 (16)	0.22234 (6)	0.38327 (16)	0.0295 (3)
O2	0.57654 (19)	0.39444 (8)	0.65655 (16)	0.0367 (4)
O3	0.38342 (15)	0.46132 (7)	0.51578 (19)	0.0351 (4)
C1	0.4869 (2)	0.33848 (9)	0.4394 (2)	0.0256 (4)
C2	0.3939 (2)	0.33602 (9)	0.3211 (2)	0.0262 (4)
C3	0.3171 (2)	0.38737 (10)	0.2398 (2)	0.0294 (5)
H3	0.3221	0.4377	0.2585	0.035*
C4	0.2358 (2)	0.36252 (10)	0.1336 (2)	0.0321 (5)
H4	0.1835	0.3965	0.0784	0.039*
C5	0.2264 (2)	0.28691 (11)	0.1021 (2)	0.0316 (5)
C6	0.1433 (3)	0.26263 (12)	−0.0094 (2)	0.0399 (6)
H6	0.0923	0.2967	−0.0653	0.048*
C7	0.1359 (3)	0.18989 (13)	−0.0374 (3)	0.0475 (6)
H7	0.0807	0.1740	−0.1130	0.057*
C8	0.2087 (3)	0.13917 (11)	0.0444 (3)	0.0447 (6)
H8	0.2016	0.0891	0.0240	0.054*
C9	0.2901 (3)	0.16034 (10)	0.1534 (3)	0.0371 (5)
H9	0.3390	0.1253	0.2084	0.044*
C10	0.3008 (2)	0.23490 (9)	0.1835 (2)	0.0294 (5)
C11	0.3834 (2)	0.26340 (9)	0.2913 (2)	0.0276 (4)
C12	0.5250 (2)	0.26895 (10)	0.4729 (2)	0.0286 (4)
C13	0.6087 (3)	0.23448 (11)	0.5836 (3)	0.0382 (5)
H13A	0.6786	0.1949	0.5524	0.057*
H13B	0.5266	0.2151	0.6435	0.057*
H13C	0.6764	0.2706	0.6281	0.057*
C14	0.6915 (2)	0.45978 (9)	0.4545 (2)	0.0251 (4)
C15	0.8504 (2)	0.44194 (10)	0.4931 (2)	0.0304 (5)
H15	0.8679	0.4059	0.5572	0.036*
C16	0.9823 (3)	0.47724 (12)	0.4372 (3)	0.0386 (5)
H16	1.0917	0.4664	0.4624	0.046*
C17	0.9511 (3)	0.52791 (13)	0.3451 (3)	0.0423 (6)
C18	0.7955 (3)	0.54585 (13)	0.3041 (3)	0.0455 (6)
H18	0.7794	0.5813	0.2388	0.055*
C19	0.6633 (3)	0.51109 (11)	0.3605 (2)	0.0359 (5)
H19	0.5544	0.5224	0.3346	0.043*

	U11	U22	U33	U12	U13	U23
S1	0.0226 (2)	0.02804 (19)	0.0279 (3)	0.00002 (15)	0.0020 (3)	−0.0023 (2)
F1	0.0527 (9)	0.1072 (12)	0.0483 (10)	−0.0428 (9)	0.0082 (9)	0.0102 (10)
O1	0.0281 (7)	0.0237 (6)	0.0368 (9)	0.0001 (5)	0.0003 (6)	0.0019 (6)
O2	0.0381 (8)	0.0429 (7)	0.0291 (9)	−0.0014 (6)	0.0014 (8)	0.0032 (7)
O3	0.0239 (6)	0.0338 (6)	0.0477 (11)	0.0044 (5)	0.0033 (8)	−0.0078 (8)
C1	0.0223 (8)	0.0251 (8)	0.0293 (12)	−0.0009 (6)	0.0016 (9)	−0.0008 (9)
C2	0.0229 (9)	0.0256 (8)	0.0301 (12)	−0.0012 (7)	0.0028 (9)	−0.0025 (8)
C3	0.0295 (10)	0.0241 (8)	0.0344 (13)	−0.0008 (7)	0.0016 (9)	−0.0006 (8)
C4	0.0329 (10)	0.0325 (8)	0.0310 (13)	0.0016 (8)	0.0001 (10)	0.0035 (9)
C5	0.0257 (10)	0.0358 (10)	0.0332 (12)	−0.0049 (8)	0.0040 (9)	−0.0025 (9)
C6	0.0381 (11)	0.0440 (12)	0.0375 (14)	−0.0043 (9)	0.0003 (10)	−0.0036 (10)
C7	0.0465 (13)	0.0545 (14)	0.0416 (15)	−0.0139 (10)	0.0016 (13)	−0.0153 (12)
C8	0.0481 (12)	0.0354 (9)	0.0506 (17)	−0.0112 (9)	0.0099 (14)	−0.0125 (12)
C9	0.0361 (11)	0.0291 (9)	0.0459 (15)	−0.0062 (8)	0.0074 (11)	−0.0035 (10)
C10	0.0263 (9)	0.0275 (9)	0.0346 (12)	−0.0032 (7)	0.0077 (9)	−0.0040 (8)
C11	0.0239 (9)	0.0252 (8)	0.0338 (11)	−0.0008 (7)	0.0039 (9)	0.0013 (8)
C12	0.0227 (9)	0.0297 (9)	0.0335 (12)	−0.0007 (7)	0.0036 (9)	0.0019 (9)
C13	0.0352 (11)	0.0347 (10)	0.0448 (15)	0.0048 (9)	−0.0024 (11)	0.0075 (10)
C14	0.0219 (8)	0.0271 (8)	0.0263 (11)	−0.0021 (7)	0.0002 (8)	−0.0029 (8)
C15	0.0263 (9)	0.0306 (9)	0.0343 (13)	0.0027 (7)	−0.0029 (8)	−0.0025 (8)
C16	0.0252 (9)	0.0505 (12)	0.0400 (15)	−0.0028 (8)	−0.0008 (10)	−0.0093 (12)
C17	0.0389 (12)	0.0574 (13)	0.0307 (14)	−0.0206 (10)	0.0064 (11)	−0.0057 (12)
C18	0.0508 (14)	0.0525 (12)	0.0333 (14)	−0.0185 (11)	−0.0082 (12)	0.0124 (12)
C19	0.0355 (11)	0.0384 (9)	0.0339 (13)	−0.0074 (8)	−0.0086 (10)	0.0057 (10)

S1—O2	1.4313 (18)	C7—H7	0.9500
S1—O3	1.4375 (13)	C8—C9	1.366 (4)
S1—C1	1.736 (2)	C8—H8	0.9500
S1—C14	1.7596 (19)	C9—C10	1.413 (2)
F1—C17	1.348 (2)	C9—H9	0.9500
O1—C12	1.364 (3)	C10—C11	1.406 (3)
O1—C11	1.378 (3)	C12—C13	1.478 (3)
C1—C12	1.365 (3)	C13—H13A	0.9800
C1—C2	1.442 (3)	C13—H13B	0.9800
C2—C11	1.377 (2)	C13—H13C	0.9800
C2—C3	1.414 (3)	C14—C19	1.378 (3)
C3—C4	1.364 (3)	C14—C15	1.394 (3)
C3—H3	0.9500	C15—C16	1.384 (3)
C4—C5	1.434 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.360 (4)
C5—C6	1.412 (3)	C16—H16	0.9500
C5—C10	1.414 (3)	C17—C18	1.377 (3)
C6—C7	1.374 (3)	C18—C19	1.382 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.395 (4)	C19—H19	0.9500
O2—S1—O3	119.22 (11)	C11—C10—C9	124.7 (2)
O2—S1—C1	108.75 (9)	C11—C10—C5	115.16 (16)
O3—S1—C1	106.18 (9)	C9—C10—C5	120.2 (2)
O2—S1—C14	108.11 (10)	C2—C11—O1	110.52 (19)
O3—S1—C14	107.71 (9)	C2—C11—C10	124.85 (19)
C1—S1—C14	106.15 (10)	O1—C11—C10	124.62 (15)
C12—O1—C11	107.39 (14)	O1—C12—C1	109.55 (19)
C12—C1—C2	107.83 (17)	O1—C12—C13	115.41 (16)
C12—C1—S1	126.42 (18)	C1—C12—C13	135.0 (2)
C2—C1—S1	125.49 (14)	C12—C13—H13A	109.5
C11—C2—C3	119.37 (19)	C12—C13—H13B	109.5
C11—C2—C1	104.71 (18)	H13A—C13—H13B	109.5
C3—C2—C1	135.91 (17)	C12—C13—H13C	109.5
C4—C3—C2	118.08 (16)	H13A—C13—H13C	109.5
C4—C3—H3	121.0	H13B—C13—H13C	109.5
C2—C3—H3	121.0	C19—C14—C15	121.31 (19)
C3—C4—C5	122.4 (2)	C19—C14—S1	120.18 (15)
C3—C4—H4	118.8	C15—C14—S1	118.50 (16)
C5—C4—H4	118.8	C16—C15—C14	119.3 (2)
C6—C5—C10	118.56 (18)	C16—C15—H15	120.3
C6—C5—C4	121.3 (2)	C14—C15—H15	120.3
C10—C5—C4	120.1 (2)	C17—C16—C15	118.2 (2)
C7—C6—C5	120.2 (2)	C17—C16—H16	120.9
C7—C6—H6	119.9	C15—C16—H16	120.9
C5—C6—H6	119.9	F1—C17—C16	118.5 (2)
C6—C7—C8	120.6 (2)	F1—C17—C18	117.9 (2)
C6—C7—H7	119.7	C16—C17—C18	123.6 (2)
C8—C7—H7	119.7	C17—C18—C19	118.4 (2)
C9—C8—C7	121.1 (2)	C17—C18—H18	120.8
C9—C8—H8	119.4	C19—C18—H18	120.8
C7—C8—H8	119.4	C14—C19—C18	119.2 (2)
C8—C9—C10	119.4 (2)	C14—C19—H19	120.4
C8—C9—H9	120.3	C18—C19—H19	120.4
C10—C9—H9	120.3
O2—S1—C1—C12	−10.6 (2)	C1—C2—C11—C10	179.16 (19)
O3—S1—C1—C12	−140.05 (17)	C12—O1—C11—C2	−0.1 (2)
C14—S1—C1—C12	105.50 (18)	C12—O1—C11—C10	−179.04 (19)
O2—S1—C1—C2	162.76 (16)	C9—C10—C11—C2	−179.9 (2)
O3—S1—C1—C2	33.3 (2)	C5—C10—C11—C2	0.6 (3)
C14—S1—C1—C2	−81.12 (18)	C9—C10—C11—O1	−1.1 (3)
C12—C1—C2—C11	−0.3 (2)	C5—C10—C11—O1	179.34 (18)
S1—C1—C2—C11	−174.67 (15)	C11—O1—C12—C1	−0.1 (2)
C12—C1—C2—C3	178.4 (2)	C11—O1—C12—C13	177.31 (18)
S1—C1—C2—C3	4.0 (3)	C2—C1—C12—O1	0.2 (2)
C11—C2—C3—C4	−0.4 (3)	S1—C1—C12—O1	174.55 (14)
C1—C2—C3—C4	−178.9 (2)	C2—C1—C12—C13	−176.4 (2)
C2—C3—C4—C5	−0.2 (3)	S1—C1—C12—C13	−2.1 (3)
C3—C4—C5—C6	−179.1 (2)	O2—S1—C14—C19	−152.63 (17)
C3—C4—C5—C10	1.0 (3)	O3—S1—C14—C19	−22.6 (2)
C10—C5—C6—C7	−0.1 (3)	C1—S1—C14—C19	90.83 (18)
C4—C5—C6—C7	−180.0 (2)	O2—S1—C14—C15	26.78 (19)
C5—C6—C7—C8	0.6 (4)	O3—S1—C14—C15	156.85 (16)
C6—C7—C8—C9	−0.5 (4)	C1—S1—C14—C15	−89.76 (18)
C7—C8—C9—C10	−0.1 (3)	C19—C14—C15—C16	1.0 (3)
C8—C9—C10—C11	−178.9 (2)	S1—C14—C15—C16	−178.42 (17)
C8—C9—C10—C5	0.7 (3)	C14—C15—C16—C17	−0.6 (3)
C6—C5—C10—C11	179.01 (19)	C15—C16—C17—F1	178.8 (2)
C4—C5—C10—C11	−1.1 (3)	C15—C16—C17—C18	−0.2 (4)
C6—C5—C10—C9	−0.6 (3)	F1—C17—C18—C19	−178.3 (2)
C4—C5—C10—C9	179.30 (19)	C16—C17—C18—C19	0.7 (4)
C3—C2—C11—O1	−178.73 (17)	C15—C14—C19—C18	−0.5 (3)
C1—C2—C11—O1	0.2 (2)	S1—C14—C19—C18	178.88 (18)
C3—C2—C11—C10	0.2 (3)	C17—C18—C19—C14	−0.3 (4)

Cg1 is the centroid of the C14–C19 4-fluorophenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3i	0.95	2.46	3.379 (2)	163
C15—H15···F1ii	0.95	2.53	3.150 (3)	123
C16—H16···O3iii	0.95	2.44	3.380 (2)	170
C4—H4···Cg1iv	0.95	2.75	3.625 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 4-fluoro­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O3i	0.95	2.46	3.379 (2)	163
C15—H15⋯F1ii	0.95	2.53	3.150 (3)	123
C16—H16⋯O3iii	0.95	2.44	3.380 (2)	170
C4—H4⋯Cg1iv	0.95	2.75	3.625 (3)	154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .